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One of my colleagues ruptured her eardrum from flying during an ear infection. She had to be carried off the plane because she temporarily lost her sense of balance (on top of terrible pain before it burst, and temporary loss of hearing). Once the eardrum bursts, the pain stops, but why do that to a kid? A burst eardrum will heal, but scarring from it might mess with your hearing for life.

The duration of the flight is irrelevant, it's the pressure increase during landing that matters.

DD's eardrum burst in the ER a few months ago. We took her in because she was in so much pain in the middle of the night. We were with the doctor and she suddenly screamed and then we actually heard a POP and then she was fine. The doctor said he'd never actually heard one pop before like that. She was fine. And her ear healed itself. Lots of kids do fly with ear infections, it's one of those tricky judgement call things.